Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H17Cl2NO2 |
Molecular Weight | 314.207 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C3=CC(Cl)=CC(Cl)=C3
InChI
InChIKey=MNJNPLVXBISNSX-WDNDVIMCSA-N
InChI=1S/C15H17Cl2NO2/c1-18-12-2-3-13(18)8-14(7-12)20-15(19)9-4-10(16)6-11(17)5-9/h4-6,12-14H,2-3,7-8H2,1H3/t12-,13+,14+
Bemesetron, also known as MDL 72222, is a potent and highly selective antagonist of neuronal 5-hydroxytryptamine receptors, 5HT3. Bemesetron possesses antiemetic efficacy in comparison with a high-dose metoclopramide regimen (HDM) for chemotherapy-induced nausea and vomiting. But this application is not clinically used. Drug is used as scientific tool for the study 5HT3 receptor properties in the actions of drugs of abuse.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1314791
Curator's Comment: Known to be CNS non-penetrant in rat. Human data not available
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094132 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3114804 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Serotonin and NO complementarily regulate generation of oscillatory activity in the olfactory CNS of a terrestrial mollusk. | 2001 Jun |
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5-HT2 and 3 receptor antagonists suppress the response of rat type I slowly adapting mechanoreceptor: an in vitro study. | 2003 Apr 18 |
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Conditional involvement of striatal serotonin3 receptors in the control of in vivo dopamine outflow in the rat striatum. | 2003 Feb |
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Pretreatment with serotonin 5-HT(3) receptor antagonists produces no observable blockade of long-term motor sensitization to cocaine in rats. | 2003 Feb |
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The serotonin type 3A receptor facilitates luteinizing hormone release and LHbeta promoter activity in immortalized pituitary gonadotropes. | 2005 Jun |
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Rewarding properties of 1-benzylpiperazine, a new drug of abuse, in rats. | 2006 Apr |
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Involvement of 5-HT receptors in the development and expression of methamphetamine-induced behavioral sensitization: 5-HT receptor channel and binding study. | 2006 Nov |
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5-HT3 receptor-dependent modulation of respiratory burst frequency, regularity, and episodicity in isolated adult turtle brainstems. | 2010 Jun 30 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8452114
MDL 72,222 (Bemesetron) was given in 20 mg intravenous doses 30 minutes before chemotherapy, as well as 2, 6, and 12 hours after chemotherapy infusion
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6472484
The properties of MDL 72222 (bemesetron) with potent and selective blocking actions at certain excitatory 5-hydroxytryptamine (5-HT) receptors on mammalian peripheral neurones, are described. On the rabbit isolated heart, MDL 72222 was a potent antagonist of responses mediated through the receptors for 5-HT present on the terminal sympathetic fibres. The threshold for antagonism was approximately 0.1 nM and the negative logarithm of the molar concentration of MDL 72222 which reduced the chronotropic response of the isolated rabbit heart to twice an ED50 of 5-HT to that of the ED50 was 9.27. MDL 72222 was also highly selective since responses to the nicotine receptor agonist, dimethylphenylpiperazinum iodine (DMPP), were inhibited only at concentrations more than 1000 times those necessary to inhibit 5-HT.
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NCI_THESAURUS |
C94726
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C042253
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Bemesetron
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DTXSID8042632
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40796-97-2
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BB-8
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CHEMBL2107804
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100000086139
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SUB05692MIG
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6682
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C80766
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O98T3677PA
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ACTIVE MOIETY